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I know this question is dangerously close to asking for legal advice, but for the record I'm not planning on making any actual decision based on this answer, I would be consulting with a lawyer if I did try to set up a non profit. All I'm looking for now is a basic sanity test to determine rather what I'm considering is potentially viable and worth putting time and effort into pursuing it further.

To give context I donate a significant percentage of my, fairly decent, income to charity. I also currently have a large nest egg of money, numerous factors including two separate inheritances and a large investment being repaid have left me with so much money this year that ironically I'm having trouble donating it all, I would only be able to get tax refund on a fraction of it, and since I already donate close to the maximum I can claim on taxes every year anyways even carrying those donations into future years could take well over a decade to claim all the tax savings.

I've instead been toying with the idea of buying a large rental property, one with multiple bedrooms I could rent out to individuals as an investment. I'd also likely stay in the smallest of the rooms myself, I'm too cheap to pay for a real home and at least if I own the rental property I can't get kicked out and forced to move again if a family needs their room back. Unfortunately the added rental income, which would be donated to charity, would likely again push me over the amount I can claim for charitable donations in my taxes.

So I was toying with the idea of buying a property but registering it as a non-profit so all the rental income is immediately untaxed, I'd then funnel the money the rental made to the charity I support (givewell.com, the most efficient way to save lives!). I'd presumably be paying a lawyer to set up the non-profit but that's a one time fee I can deal with. I'm more worried about what the logistical effort it would create for me to be maintaining a rental property as a non profit. I presume I'd have to keep my personal finances and the rental property finances separate, but is it as simple as having separate bank accounts or do I need to do more to prove I'm not profiting from the property? Would I still be able to live at the property as one of the renters, paying appropriate rent to the non-profit, or would that create a conflict of interest even if I was paying reasonable rental amounts?

To be frank I'm not the most organized and part of the reason I've put off buying property before is I didn't want to take on all the logistical hassle of being a landlord. If having a rental property registered as a non-profit adds too much additional overhead I may give up on both ideas and just stick to donating all the money to charity as I have been. So before I go digging too deep into the process can anyone give me a rough idea of what hassles I'd be taking on if I tried to go down this route?

Both I and the rental I would purchase would be located in Maryland, USA.

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Would I still be able to live at the property as one of the renters, paying appropriate rent to the non-profit, or would that create a conflict of interest even if I was paying reasonable rental amounts?

You could, though you might need to have some sort of valuation to back up the fair market value assessment.

Honestly, it would probably be fair easier to just make charitable donations of the portion of the rent received you want to donate and to consider a charitable donation upon the sale of the property or your death in your will if you are so inclined.

The only upside would be to avoid paying property taxes, but property taxes are a tax deductible expense and as a non-profit the ongoing management of the building would be complicated and require work with an attorney on a regular basis to confirm that compliance continues.

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